Quantitative Structure-activity Relationships of Benzoyl (pyridyloxyphenyl) urea Insecticides

Haga, Takahiro; Toki, Tadaaki; Koyanagi, Tohru; Nishiyama, Ryuzo

doi:10.1584/jpestics.10.217

Cited by 24 publications

(17 citation statements)

References 2 publications

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“…The search for potent acylureas has led to the development of new compounds such as chlorfluazuron (Haga et al, 1982), teflubenzuron (Becher et al, 1983), and hexaflumuron (Sbragia et al, 1983), which are far more potent than diflubenzuron on various agricultural pests (Ishaaya, 1990). One of the recent benzoylphenyl ureas, which is in the process of commercialization and use, is novaluron April 2005 {Rimon EC-10, 1-[chloro-4-(1,1,2-trifluoromethoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea}.…”

Section: Introductionmentioning

confidence: 99%

Biorational insecticides: Mechanism and cross‐resistance

Ishaaya

Kontsedalov

Horowitz

2005

Arch Insect Biochem Physiol

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Potency and cross-resistance of various biorational insecticides, exemplified by the whitefly Bemisia tabaci, have been studied. Bemisia tabaci were exposed to the juvenile hormone mimic pyriproxyfen for the past 12 years resulting in an over 2,000-fold resistance, but there was no appreciable cross-resistance with the benzoylphenyl urea novaluron. Similarly, no cross-resistance was found between pyriproxyfen and the two neonicotinoids, acetamiprid and imidacloprid. On the other hand, a slight cross-resistance of 5-13-fold was observed with another neonicotinoid thiamethoxam. Among the neonicotinoids, a resistant strain of B. tabaci to thiamethoxam (approximately 100-fold) showed no appreciable cross-resistance to either acetamiprid or imidacloprid, while another strain 500-fold resistant to thiamethoxam resulted in a mild of 4-6-fold resistance to acetamiprid and imidacloprid. In other assays, B. tabaci strain resistant to thiamethoxam (approximately 100-fold) had no cross-resistance to pyriproxyfen. Our findings indicate that no appreciable cross-resistance was observed between the benzoylphenyl urea novaluron, the juvenile hormone mimic pyriproxyfen, and the neonicotinoids acetamiprid and imidacloprid. Hence, these compounds could be used as components in insecticide resistance management programs.

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Section: Introductionmentioning

confidence: 99%

Biorational insecticides: Mechanism and cross‐resistance

Ishaaya

Kontsedalov

Horowitz

2005

Arch Insect Biochem Physiol

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“…Those which have a fluorine, chlorine or methyl group at the 2-position were most effective, and these substituents at this position may have good balance with 4-S (O)m-CF2CFXH groups from viewpoints of substituent effects which may affect the stability of the compounds against metabolic degradation in the larval body. [19][20][21] Larvae which had fed on leaves treated with test compounds showed the same symptoms as caused by known benzoylphenylurea compounds: they failed to shed the old curticle and died during moulting.…”

Section: Resultsmentioning

confidence: 89%

Synthesis and Insecticidal Activity of Novel 1-Benzoyl-3-phenylurea Derivatives with Polyfluoroethylsulfenyl, -sulfonyl, and-sulfinyl Substituents

et al. 1992

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In the course of modifying substituents on the 3-phenyl moiety of 1-benzoyl-3-phenylurea compounds known as potent insect growth regulators, we prepared those having polyfluoroethylsulfenyl, -sulfinyl, and -sulfonyl substituents at the 4-position and second ones (halogen, methyl) at other positions, and investigated their larvicidal activity against lepidopterous insects.Most of sulfenyl derivatives (4) had the excellent activity as we had expected, and to our surprise some of sulfonyl (2) and sulfinyl derivatives (3) also showed effectiveness comparable to that of 4. It was considered the larvicidal activity of these compounds was enhanced under good balance of key substituents at the 4-position and additional ones at the 2-position on the 3-phenyl ring system.

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“…The search for potent acylureas has led to the development of new compounds such as chlorfluazuron (Haga et al 1982), teflubenzuron (Becher et al 1983) and hexaflumuron (Sbragia et al 1983), which are far more potent than diflubenzuron on various agricultural pests (Ishaaya 1990). One of the recent benzoylphenyl ureas, which is in the process of commercialization, is novaluron {Rimon EC-lO, 1-[chloro-4-(I,1,2-trifluoromethoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea}.…”

Section: Chitin Synthesis Inhibitionmentioning

confidence: 99%

Biochemical Processes Related to Insecticide Action: an Overview

Ishaaya

2001

Biochemical Sites of Insecticide Action and Resistance

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Quantitative Structure-activity Relationships of Benzoyl (pyridyloxyphenyl) urea Insecticides

Cited by 24 publications

References 2 publications

Biorational insecticides: Mechanism and cross‐resistance

Biorational insecticides: Mechanism and cross‐resistance

Synthesis and Insecticidal Activity of Novel 1-Benzoyl-3-phenylurea Derivatives with Polyfluoroethylsulfenyl, -sulfonyl, and-sulfinyl Substituents

Biochemical Processes Related to Insecticide Action: an Overview

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